So I'm a guitarist (electric) and I've moved from Cubase to Live, and I've run into this problem tracking guitars. The recording of my guitar always end up being late on the timeline and I keep having to slightly advance the recording towards the beginning of the track afterwards to get it to play in time :O Is there a simple way to make the track automatically sync up with the other tracks as I played it while recording?

I don't know for certain, I use Sonar, but it sounds like you might have a sound card latency issue or latency in whatever mixer or hardware you're using to get sound in/out.
If so you'll hear the playback tracks a few milliseconds later than the software is playing them, and that's what you're recording the guitar track to._________________I heard they threatened Tokai with a lawsuit, but they never got to Cort?